Binary and ternary cocrystals of sulfa drug acetazolamide with pyridine carboxamides and cyclic amides

Geetha Bolla, Ashwini Nangia

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

A novel design strategy for cocrystals of a sulfonamide drug with pyridine carboxamides and cyclic amides is developed based on synthon identification as well as size and shape match of coformers. Binary adducts of acetazolamide (ACZ) with lactams (valerolactam and caprolactam, VLM, CPR), cyclic amides (2-pyridone, labeled as 2HP and its derivatives MeHP, OMeHP) and pyridine amides (nicotinamide and picolinamide, NAM, PAM) were obtained by manual grinding, and their single crystals by solution crystallization. The heterosynthons in the binary cocrystals of ACZ with these coformers suggested a ternary combination for ACZ with pyridone and nicotinamide. Novel supramolecular synthons of ACZ with lactams and pyridine carboxamides are reported together with binary and ternary cocrystals for a sulfonamide drug. This crystal engineering study resulted in the first ternary cocrystal of acetazolamide with amide coformers, ACZ-NAM-2HP (1:1:1).

Original languageEnglish
Pages (from-to)152-160
Number of pages9
JournalIUCrJ
Volume3
DOIs
StatePublished - 1 Jan 2016
Externally publishedYes

Keywords

  • co-crystals
  • crystal design
  • crystal engineering
  • hydrogen bonding
  • pharmaceutical solids

ASJC Scopus subject areas

  • General Chemistry
  • Biochemistry
  • General Materials Science
  • Condensed Matter Physics

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